(3-methoxyphenyl)(9H-pyrido[3,4-b]indol-1-yl)methanone | 1275575-69-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: (3-methoxyphenyl)(9H-pyrido[3,4-b]indol-1-yl)methanone
• 英文别名: (9H-β-carbolin-1-yl)-(3-methoxyphenyl)-methanone；(3-methoxyphenyl)-(9H-pyrido[3,4-b]indol-1-yl)methanone
• CAS: 1275575-69-3
• 化学式: C₁₉H₁₄N₂O₂
• 分子量: 302.332
• InChiKey: OBWNFFHSKPZZSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3-methoxyphenyl)(9H-pyrido[3,4-b]indol-1-yl)methanone 、 乙酸酐 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 12.0h， 以77%的产率得到4-(3-methoxyphenyl)-6H-indolo[3,2,1-de][1,5]naphthyridin-6-one
  参考文献：
  名称：

  碘介导的Pictet-Spengler氧化反应，使用末端炔烃作为2-氧醛代用品来合成1-芳酰基-β-咔啉和稠合氮杂环

  摘要：

  一种有效的碘介导的二甲基亚砜（DMSO）中碘介导的氧化Pictet-Spengler反应，使用末端炔烃作为2-氧醛替代物来合成芳基（9 H-吡啶并[3,4- b ]吲哚-1-基）甲烷酮。描述。该方案的范围包括法西林蛋白酶，大黄素（Eusoditomins）Y 1和Y 2的总合成。该方法扩展了制备吡咯并[1,2- a ]-喹喔啉和吲哚并[1,5- a ]喹喔啉衍生物的方法。1-芳酰基-β-咔啉的实用性通过执行钯催化的β-咔啉直接邻位得到证明-C（sp2）-H使用DMSO作为来源和访问4-芳基-canthin-6-ones的硫代甲基（SMe）基团对苯环的官能化。

  DOI：

  10.1016/j.tet.2017.03.031
• 作为产物：
  描述：

  3-甲氧基苯基乙二醛水合物 、 L-色氨酸 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以15%的产率得到(3-methoxyphenyl)(9H-pyrido[3,4-b]indol-1-yl)methanone
  参考文献：
  名称：

  Synthesis, in vitro anti-inflammatory and cytotoxic evaluation, and mechanism of action studies of 1-benzoyl-β-carboline and 1-benzoyl-3-carboxy-β-carboline derivatives

  摘要：

  In the present study, various 1-substituted and 1,3-disubstituted beta-carboline derivatives were synthesized by a modified single-step Pictet-Spengler reaction. The compounds were examined for cytotoxicity and anti-inflammatory activity, as measured by the inhibition of prostaglandin E-2 (PGE(2)) production and nitric oxide (NO) production. While only two compounds (28 and 31) showed marginal cytotoxicity against four human cancer cell lines, most of the tested compounds exhibited potent inhibitory activity of both NO and PGE(2) production. Moreover, compounds 6 and 16 significantly reduced the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase 2 (COX2), suggesting that beta-carboline analogs can inhibit NO and PGE(2) production at the translational level. In addition, several of the beta-carboline derivatives (1, 2, 48, 11, 13, 22, 25, 27, 31, and 41-43) displayed significant inhibitory activity of superoxide anion (O-2(center dot-)) generation or elastase release compared to the reference compound, with 6 being the most potent. N-Formyl-L-methionyl-phenylalanine (FMLP)-induced phosphorylation of c-Jun N-terminal kinase (JNK) and protein kinase B (AKT) were also inhibited by 6, suggesting that it suppresses human neutrophil functions by inhibiting the activation of JNK and AKT signaling pathways. Therefore, the synthetic 1-benzoyl-3-carboxy beta-carboline analogs may have great potential to be developed as anti-inflammatory agents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.01.034

文献信息

• β-Carboline-directed decarboxylative acylation of ortho-C(sp²)–H of the aryl ring of aryl(β-carbolin-1-yl)methanones with α-ketoacids under palladium catalysis
  作者：Shivalinga Kolle、Sanjay Batra

  DOI：10.1039/c6ra11811a

  日期：——

  A palladium-catalysed β-carboline directed decarboxylative acylation of ortho-C(sp2)–H of the aryl ring of aryl(β-carbolin-1-yl)methanones using α-oxocarboxylic acid as the acyl ion equivalent to form (2-aroylaryl)(β-carbolin-2-yl)methanones is described. The utility of these products for preparing β-carboline-tethered phthalazine systems is also demonstrated.

  以α-氧代羧酸为等效形式的钯催化的β-咔啉对芳基（β-carbolin-1-yl）甲酮的芳基环的邻-C（sp 2）-H进行直接脱羧酰化（2描述了-（芳酰基芳基）（β-咔啉-2-基）甲酮。还证明了这些产品在制备β-咔啉系酞菁体系中的实用性。
• A New Mild Method for Synthesis of Marine Alkaloid Fascaplysin and Its Therapeutically Promising Derivatives
  作者：Oleg A. Tryapkin、Alexey V. Kantemirov、Sergey A. Dyshlovoy、Vladimir S. Prassolov、Pavel V. Spirin、Gunhild von Amsberg、Maria A. Sidorova、Maxim E. Zhidkov

  DOI：10.3390/md21080424

  日期：——

  addition, the number of methods for the syntheses of its derivatives is limited. In the current study, we report a new two-step method of synthesis of fascaplysin derivatives based on low temperature UV quaternization for the synthesis of thermolabile 9-benzyloxyfascaplysin and 6-tert-butylfascaplysin. 9-Benzyloxyfascaplysin was used as the starting compound to obtain 9-hydroxyfascaplysin. However

  Fascaplysin 是一种海洋生物碱，由于其多样化且有效的生物活性而被认为是主要候选药物。作为一种抗癌剂，fascaplysin 具有巨大的潜力，因为这种生物碱在癌细胞中影响多个靶点，包括抑制细胞周期蛋白依赖性激酶 4 (CDK4) 和诱导内在细胞凋亡。同时，其结构优化的研究也因其较高的毒性（主要是由DNA嵌入引起）而受到阻碍。此外，其衍生物的合成方法数量有限。在目前的研究中，我们报道了一种基于低温紫外季铵化的新型两步法 fascaplysin 衍生物合成方法，用于合成不耐热的 9-benzyloxyfascaplysin 和 6-tert-丁基 fascaplysin。使用9-苄氧基fascaplysin作为起始化合物以获得9-羟基fascaplysin。然而，发现后者在化学上高度不稳定。与 fascaplysin 相比，6-tert-Butylfascaplysin 的 DNA 嵌